28 Questions With Hugh Hefner

Quick Bio

A Chicago native, Hugh Hefner served in the U.S. Army before enrolling in the University of Illinois at Urbana-Champaign. After graduation, he worked as a copywriter for Esquire magazine while raising money to launch his own publication: Playboy. The first issue featured none other than sexy siren Marilyn Monroe.

In 1959 Hugh Hefner divorced his wife of 10 years (and mother of his two children), Mildred Williams. He continued heading Playboy as a bachelor until 1989, when he married Kimberley Conrad, Playmate of the Year, who he would go on to have two more children with her. They separated in ’99 (although they still haven’t officially divorced).

In 2005, reality TV invaded the Playboy Mansion when the E! network launched The Girls Next Door, a reality-based show that followed around three of Hef’s main girlfriends -- Holly Madison, Bridget Marquardt and Kendra Wilkinson. TGND entered its fifth season in October 2008.

AM was invited to the Playboy Mansion to sit down with the man himself to discuss the history of the magazine, the future of the mansion, Sarah Palin, and why it's OK for an 82-year-old man to date 20-year-old women .

Mr. Playboy is your first authorized biography. Why did you wait so long?

Hugh Hefner: Well, I think the moment was right, but it also has to do with the right man coming along. I mean, [author] Steven Watts had done two previous books on men that defined the 20th century; the first on Henry Ford and the second on Disney. I was the third.

What’s the biggest misconception you think the book cleared up?

HH: Well that depends on the reader -- the book is not only a reflection of who I am but also of who people think I am. The perceptions and misconceptions of me are very much related to the prejudices and fantasies of the world around me. When you are dealing with sex, wealth and beautiful ladies, these are subjects that go deep into the American psyche Because we are essentially still [a Puritan people], we love all things sexual but still have a lot of shame and guilt related to sex. That’s what Playboy has been all about.

You have been an icon for so many men. Who were your icons?

HH: The people who had the most impact on me when I was young were Freud and Darwin, but growing up I also had my film idols. I was very influenced by the musicals and romantic comedies of the 1930s. I admired Gene Harlow and such, which probably explains why, since the end of my marriage, I’ve dated nothing but a succession of blondes (laughs).

Were you ever star-struck when you started to get traction with the magazine?

HH: Without question, the very people that I had idolized were now hanging out with me, such as Louis Armstrong. For our 5th anniversary, we hosted what became the single greatest weekend festival of jazz, and everybody was there, all the guys I idolized. And of course that continued as the magazine grew in stature, and I found myself rubbing elbows with Sinatra, Tony Curtis, etc. All of them wanted to hang out (laughs).

In the '80s, you had a string of problems - legal, political, and financial. Did you ever think of quitting, retiring and leading a quiet normal life?

HH: Never, no. You know the business aspects of the company never really interested me as long as we had the money to do the things I wanted to do. For me, the magazine was always the heart of what my life was all about, and the other half was living the life. The business end didn’t have a really big meaning, but there is no question that after success and prosperity in the '50s, '60s and '70s, there was a backlash. The '80s and a major part of the '90s presented a conservative backlash against Playboy, and a lot of the changes that took place in the '60s and '70s were resented by more conservative elements of society. Hopefully all that is going to change now with someone new in the White House (laughs).

How are Playmates different today than how they were 55 years ago?

HH: I think they are essentially the same. All women are different, so, invariably, all Playmates are also going to be different. Women today are healthier, taller and take better care of themselves, probably use a little more silicone (laughs) but essentially they are the same. The difference between Marilyn Monroe and the early Pamela Anderson is not that great. What’s amazing is that the taste of American men and international tastes in terms of beauty have essentially stayed the same. Styles change, but our view of beauty stays the same.

Who is the sexiest woman you’ve met in the last 55 years?

HH: (Laughs) The mind boggles. I have no idea. (Continues laughing) Probably the last one.

How involved are you with getting celebrities to pose for Playboy? Did you ever pick up a phone to push someone over the fence?

HH: Never. Never had to. People do that for me -- I’ve never made a call.

How did The Girls Next Door get started?

HH: Well, with the popularity of reality shows, a lot of people approached us with a notion of doing a reality show. There has been an ongoing fascination with my life and the life at the Playboy Mansion, and I had turned those [previous] offers down because I didn’t think I had the time for it. The decision to do The Girls Next Door came because I had faith in the producer, Kevin Burns, who had done a documentary on me for A&E and the inspired notion that life at the mansion would be presented through the eyes of my girlfriends. So it would take a lot of pressure and time off of me. That’s why I said yes.

And that turned out to be an absolutely inspired idea because it opened the show up to a much wider audience. The show is now global. People don’t have any idea of how wildly popular it is around the world and how it has helped the E! channel build their business overseas.

Keep reading and see what Hugh Hefner had to say about dating women a quarter his age...